2-Methoxyethylamine → tert-Butyl 4-[(2-methoxyethyl)amino]piperidine-1-carboxylate

HRID 888944Notes

Reaction equation

HRID 888944 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:15][O:16][CH2:17][CH2:18][NH2:19].[BH4-].[Na+]>CO>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:19][CH2:18][CH2:17][O:16][CH3:15])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 43652134tert-Butyl 4-[(2-methoxyethyl)amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-BOC-4-piperidone (2.00 g) and 2-methoxyethylamine (872 μl) were stirred together in methanol (20 ml) at room temperature for 12 hours. Sodium borohydride (760 mg) was added in several aliquots over 30 minutes and the reaction mixture stirred for a further 12 hours at ambient. The solvents were removed in vacuo and the residue diluted with dichloromethane (50 ml) and washed with brine and dried (MgSO4). The solvents were removed in vacuo to give a residue which was purified by flash silica chromatography to give 4-(2-methoxy-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.69 g) as a colourless oil.

Workup

  1. customThe solvents were removed in vacuo
  2. additionthe residue diluted with dichloromethane (50 ml)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvents were removed in vacuo
  6. customto give a residue which
  7. customwas purified by flash silica chromatography

Sources & evidence

ORD record
ord-8442ee7bdea2422cb62dd715fdd1d322
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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